The spirocyclopropyl moiety as a methyl surrogate in the structure of L-fucosidase and L-rhamnosidase inhibitors
Nitrogen-in-the-ring analogues of L-fucose and L-rhamnose were prepared, which feature a spirocyclopropyl moiety in place of the methyl group of the natural sugar. The synthetic route involved a titanium-mediated aminocyclopropanation of a glycononitrile as the key step. Four new spirocyclopropyl iminosugar analogues were generated, which displayed some activity towards L-fucosidase and L-rhamnosidase. (c) 2009 Elsevier Ltd. All rights reserved.
Keywords: Iminosugars ; Glycosidases ; Inhibition ; Spiro compounds ; Alpha-L-Fucosidase ; Glycosyltransferase Inhibitors ; Polyhydroxylated Pyrrolidine ; Primary Cyclopropylamines ; Glycosidase Inhibitors ; Mediated Synthesis ; Colorectal-Cancer ; Chitin Synthase ; D-Ribose ; Series
Record created on 2010-11-30, modified on 2016-08-09